© All photos courtesy of Larry Busby via Visit Gulfport Florida

Welcome to Gulfport, Florida, a largely undiscovered, intimate, and artsy enclave worth a peek.

Sizing in at just under three square miles, Gulfport, Florida, could easily be overlooked – after all, tucked just to the west of St. Petersburg, it naturally rests in the shadow of the popular Tampa/Clearwater metro area. But this former fishing village-turned-intimate, artsy enclave is worth a closer look. Not just for its candy-colored boutique-lined Beach and Shore Boulevards that serve as the heart of the historic downtown area overlooking Boca Ciega Bay, but all the other open-air activities it offers, from a legendary weekly farmers market to the 500-foot pier and even a sculpture park.

Village District


Gulfport’s unspoiled waterfront village district is brimming with independent shops, boutiques, and eateries – no parking meters, no chain stores. Stroll the brick-paved streets under a canopy of moss-draped live oaks, admire the quaint candy-colored cottages, or chat up one of the friendly locals for a true taste of the “small town with a big heart.” Once a finalist for the title of Rand McNally’s “Best Food Town” in the United States, Gulfport’s downtown boasts more than a dozen eclectic eateries offering up everything from Texas barbecue at Smokin’ J’s to authentic cooked-to-order Greek delicacies at Neptune Grill.

Clymer Park Sculpture Garden

Dedicated in 2015 as one of the largest municipal installations of public art in Pinellas County, Clymer Park Sculpture Garden features 10 works by five local artists in both Clymer Park and the neighboring Beach Boulevard Park Complex. Interspersed amid the lush landscaping complemented by extensive botanical architecture, passers-by will delight in giant ceramic chess pieces, a metal robot on bended knee, and interactive wind chimes. The serene adjoining parks feature two small boardwalks, exterior lighting, and curved brick walkways.

Gulfport Tuesday Fresh Market


Visitors flock to the historic waterfront district in Gulfport year-round for this weekly market, first established in 2006, for unique and locally produced artisan goods from 50 vendors. In addition to traditional farmers market staples, such as fruits and vegetables, prepared foods, and baked goods, you’ll also find artists and crafters (many working while you watch), live music, and local authors. Be sure to stop by Island Rum Cakes, from nearby Seminole, Florida, for a slice of their famous Butter Pecan Rum Cake.

Williams Pier

Located at the intersection of 54th Street South and Shore Boulevard, the first iteration of this pier was built in 1907, with the latest being renovated in 2001 and dedicated to husband-and-son Bert and Walter Williams (they served as city officials in the town for more than a combined 27 years). Well-lit for an evening stroll and line with benches for taking in the sunset, the best part is how long the pier is for a small town: 521 feet.

Gulfport Casino Ballroom

This iconic waterfront entertainment venue, overlooking Boca Ciega Bay, draws visitors from near and far for its swing, Latin, Argentine tango, and ballroom dancing most nights of the week. Originally built in 1906 as a ferry terminal and ticket office, the 5,000-square-foot ballroom features an authentic 1930s style hardwood dance floor and is now considered a national historic site.


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